Cupmon
by YumenianPrincess
Summary: I know worst title ever, but I couldn't think of anything. I have a theory that Jessie is Giovanni's daughter so when Jessie starts acting awkward around Giovanni now you know why. Before you say anything, I DO NOT SHIP SALLY STAGEPLAY WITH WALLY WARBLES. I think they're a terrible match. I do however ship Baroness Von Bon Bon and Grim so watch out for that. Maybe Rated M who knows
1. Chapter 1

**The Dex Holders arrive in Alola for vacation. I know this is terrible but it'll get better once I add** ** _them_** **. Blue is a girl and Green is a boy.**

 **Disclaimer: I don't own Pokémon**

The Alola region. The dex holders was on the port where the paparazzi waited. Giovanni accompanied them while the went to the Pokémon School. Ash and his friends have finished beating up James' Pokémon and Meowth. Jessie was no where to be seen. Professor Kukui welcomed the Dex Holders and even gave them desks. Blue sat next to Silver and Green. Silver smiled while Green whispered, "Pesky Woman." Red and Yellow talked to each other while Ruby, Sapphire, Emerald, Gold, and Crystal were talking to Ash's friends.

"So you've disbanded Team Rocket?" Ash said.

"Yes. If those idiots James and Meowth bother you just tell me." Giovanni said.

"What about Jessie?"

Giovanni was going to say something, then immediately shut up. He didn't say anything else after that.

Professor Kukui made them do activities. Most of them were just Pokémon battles. They all had fun until, something flew fast above them. One was a green dragon and the other was a blue bird with a house. They landed behind the school. The trainers went to investigate and found something shocking.


	2. Chapter 2

**I'll try to update regularly. I have school and my brother's annoying.**

 **Disclaimer: I don't own Cuphead**

Jessie Rocket walked towards Inkwell 2. Her pink hair was down, she wore a green shirt, pale skirt, brown boots, and of course, her blue bow. The Inkwell 2 residents were having another competition.

"Hey! Jess! Over here!" yelled Hilda Berg.

Jessie stood next to her. Hilda held Cagney's hand.

 _Tch. Of course she needs me for moral support._

Cagney tried not to look cute around Hilda but he failed. Eventually, Djimmi and Beppi came over.

"Get ready folks! We're gonna have a another wild-" Beppi said then got interrupted.

"Ja! Wir wissen! Ein anderes Luftrennen! GERADE MIT!" Werner Werman said.

Everyone looked at him confused. No one understood his language.

"JUST GET IT OVER WIZ IT!"

"Uh...okay...Anyways, this years aerial race will start here and end in Honeycomb Herald's roof!"

Djimmi was next to speak, "The competetors for this year is, Grim Matchstick from Firey Frolic-"

The crowd went wild when Grim arrived. His adorableness is too much.

"And Wally Warbles from Aviary Action!"

Not that much of them cheered for him. He didn't mind. His son was cheering for him, and that's all that he needs. Baroness Von Bon Bon took out a candy cane pistol and held it up in the air. "Ready...Set..." She fired a gumdrop. "GO!"

Everyone cheered wildly. Grim was faster than Wally but slowed down for him to catch up. They were neck and neck, until...The Devil arrived.

"Hey Dice, why don't we make this year's race interesting."

"Certainly sir."

King Dice snapped his fingers. Soon Dice's cards surrounded everyone. Jessie couldn't reach her knife in her bag. Even if she did it wouldn't make a dent in them. The only thing that could beat them was Cuphead and Mugman.

"The boss here has given me a new power. Let's test it out shall we?" Dice said.

The bosses braced themselves. Dice turned around and pointed his finger. A purple light appeared and so did a black hole. Without their mighty dragon, they could barely do anything. "Throw the candy queen in there along with the pink haired brat." Dice said.

"Are you mad Dice?! If you do that the dragon will comeback and end us!" The Devil roared.

Grim loves Bon Bon. If anything happened to her, he'll destroy them in his final phase.

"You're right. Throw the actor too."

The cards carried Bon Bon, Jessie, and Sally. Soon a fireball came out of no where and destroyed the cards, launching the three girls into the black hole. It started to rain. Grim came, in his three-headed phase, with Wally beside him.

"B-B-Bon Bon? D-Dice... I-It was a mistake to sh-show your face here ag-gain. You piece of shit."

The middle head used his flamethrower attack. The Devil used his demons to try and stop them. They soon got run over and stepped on by Werner's soup tank (I think it's a tank) and Dr. Kahl's Robot. Wally fired his three bullet missiles and regurgitated his eggs. Grim's anger got the best of him. He flew so fast he knocked Wally out of the sky and were both sucked into the black hole.

On the other side, Bon Bon, Jessie, and Sally were in another dimension. They didn't have time to look around since they were still falling. Then Grim and Wally appeared. They scooped them up and allowed them to ride on their backs. Bon Bon and Jessie on Grim and Sally on Wally. They saw a huge building and decided to land near there. Jessie was NOT excited about that.

 _FRICK! THAT"S THE POKEMON SCHOOL! ASH IS GOING TO KILL ME!_

Once they landed, they heard voices. Jessie did not expect to see _them_ again.


	3. Chapter 3

**My Jessie was the first kid to be kidnapped by the Mask of Ice.**

 **Disclaimer: I don't own Cuphead and Pokémon**

For a moment, no one said anything. Then Wally started going nuts. He was screaming and flapping his wings. None of the bosses have ever traveled to other dimensions. Bon Bon tried getting protection under Grim's wings. Sally hid behind Jessie. "Heh...heh." Jessie said.

"Heh...heh. N-Nice to see you a-again. D-Dad."

The bosses looked shocked. Where was he? The father who neglected her when she needed him most. Jessie had told Hilda Berg countless times. How the Mask of Ice trained her to be a skilled murderer. How he never bothered to go looking for her. Now there he was. Staring at his daughter who befriended interdimensional beings. She looked at each one. Her eyes finally settled on a red head boy.

 _Is this him? My brother?_

She's heard of him before, but she didn't think it was true. Finally Ash broke the ice,

"You're not getting away this time!" he shouted.

"What in the name of Arceus are you talking about? I just got here."

"I know what you're going to do! You're going to sell that green Dragonite!"

"Drago- Oh. Grim Matchstick is not a Dragonite!"

Suddenly they heard music.

watch?v=foaw2arHA50

Sally started to attack. She threw a fan at Mallow's head. Then she kicked Gold's stomach. The others didn't know what to do. Should they attack this woman or not? Then Blue sent out Blasty.

"Hydro Pump now!'

Her Blastoise fired it's attacking leaving Sally soaking wet. It did nothing.

"Pikachu, Thunderbolt!" Ash said.

Pikachu's thunder didn't do anything either. It should've hurt her more since she's soaking wet. But nothing happened. Sally started to laugh, and so did her friends.

"Nothing can hurt us except for the Cup Bros and the Ink Demon."

She kicked Ash's head, making him fall to the ground.

"Break a leg...Nah! Break two!"

She laughed as she got on Wally's back. Bon Bon and Jessie got on Grim's back, and flew away.

"What the heck...just happened?" Green said.

 _She's back. Well this vacation just got interesting..._


	4. Chapter 4

**Disclaimer: I don't own Cuphead**

After they chased Dice and Devil out of town, they tried to figure out what the heck happened. Before chasing Dice out of town, they interrogated him.

"Should we do good cop bad cop?" Blind Specter said.

Cala Maria nodded. She cleared her throat.

"Now Dice please answer this honestly... WHERE THE FUCK DID YOU BANISH OUR FRIENDS?!"

"Okay. Rumor Honeybottoms will be with you soon. Come on Cala, let's go. Byeeeeeeeeee!"

Captain Brineybeard and Rumor Honeybottoms entered the room. They tried and tried but got the same answer out of him,

"The portals I make are random, I have no control over them."

They eventually gave up and let him go. One of the Grim Matchstick Jr. from Rugged Ridge snatched up one of his gloves. Dice couldn't get it back since they were forcing him out with their powers. Cuphead and Mugman arrived from their last adventure.

"Um. Why are you guys in my house?" Cuphead said.

The bosses looked up awkwardly.

"Oh um. We just wanted to pay your old man a visit! Yeah! That's right." Djimmi said.

"What did you guys do?" Mugman said.

"Well it wasn't really us it was kind of the Devil and King Dice..." Psycarrot said.

"WHAT ABOUT THE DEVIL AND KING DICE?!"

"Let's just say Grim, Wally, Sally, Bon Bon, and Jessie were, kind of sent to another dimension, by one of Dice's new powers..." Hilda said.

"WHAT?!"

"But don't worry. We have one of Dice's gloves. I can analyze it in one of my inventions and determine what kind of power created the portal. Then we can take it to Professor Mangle at Freddy's Pizzaria and she'll create a portal to that dimension." Dr. Kahl said.

Mugman was shaking his head.

"This plan better works."

The bosses packed up and followed the path to Inkwell Isle 3. There they turned left to Junkyard Jive. Dr. Kahl's lab was full of inventions. There were also stuff Jessie brought back from other dimensions. She brought a lot of gadgets called "cell phones". Dr. Kahl took the lid off of one of his machines. "The Analyzer" it read. He placed the glove inside and flipped the switch.

To make a long story short, it blew up (I'm too lazy to describe it).

There was a piece of paper beside Ribby. He picked it up and examined it.

"Hey. This is it!"

Cuphead snatched it out of his hands.

"It says it's made of Demon Blood."

They all looked at each other. They had to show this to one more person before showing Professor Mangle.

They had to go visit, The Ink Demon.


	5. Chapter 5

**Disclaimer: I do not** **own Pokémon and Cuphead**

Giovanni tried figuring out what happened. His daughter came back from the dead.

 **-Flashback-**

 _Silver and Blue decided to stay at his house for a sleepover. Giovanni was on the phone with Lance._

 _"I'm sorry. We stormed the place and came back with this: The Mask of Ice he...he killed her."_

 _Giovanni froze. He couldn't believe this. His son escaped but why didn't his daughter?_

 _"Th-thank you. We will arrange a funeral once you b-bring back her body."_

 _"That's the thing. We didn't find a body only blood. We believe he might've burned the body."_

 _Giovanni hung up. He couldn't talk about her anymore. He finally noticed Silver and Blue._

 _"Oh. G-go upstairs. I have to do something for a while."_

 _Silver and Blue were about to when, Giovanni ran to a bathroom. They stood beside the door. All they heard was crying._

 **-Flashback end-**

The Hoenn Dex Holders and Ash were determining what Pokémon the bird and dragon were. Then there was that woman. Was she an alien? Everything that happened today was a big mystery that needs to be solved. Silver couldn't talk. He had a blood related sister that his father was hiding. Why would he do that?! He would interrogate him tomorrow. The sun was setting and they were to tired to move. So they slept in the Pokémon School.

 **HOLY SHIT IT DELETED A CHUNK OF WRITING! Sorry if this was shorter. I was to lazy to rewrite it. Don't worry I'll make it up in the next chapter.**

 **FUCK MY LIFE!**


	6. Chapter 6

**I'M BACK BITCHES! It's been like what? Two months or something. Sorry, I just wasn't sure if I should keep going. Anyways, enjoy the story!**

 **Disclaimer: I do not own Pokémon and Cuphead**

Jessie was slightly sad. "Too bad there aren't any Pokémon contests here in Alola." she said. "Ahem. Are you forgetting something?" Baroness said. Jessie looked up. They were currently in Team Rocket's crummy old hideout. "What's wrong?" "WE DON'T KNOW ANYTHING ABOUT POKEMON!" She was startled by the Baroness' sudden outburst.

"Bon Bon. Don't stress her out. She's just seen her father again in twenty years." Sally said putting an arm around the candy queen.

"Uh...I-I guess your right. Sorry Jess, it's just that...us bosses haven't really explored other dimensions. We're so used to our dimension and Dream World. Um..."

Grim curled up next to Baroness. Sally was giggling.

"Let's give them some privacy, shall we?" Sally said.

Jessie smiled and proceeded to exit the house with Sally. Once outside, they didn't realize how big Grim was. His wings were through the roof.

"Let's explore Melemele Island." Jessie said.

Both girls got on Wally and flew around.

~Meanwhile~

"Oh Grim I'm so glad I have you to talk too!" Baroness said.

She didn't see Grim blushing pink. His heart was beating fast. He loves her. He just doesn't know how to confess it. Baroness also loves him. She doesn't know how to confess either.

"Grim...um. Do you want to...go out to eat...or something?"

"S-S-S-Sure..."

 **I'm sorry. I said I'd make it longer. But there's something I want to start called Smile.**


End file.
